diff --git a/agents-api/agents_api/activities/task_steps/base_evaluate.py b/agents-api/agents_api/activities/task_steps/base_evaluate.py
index 0e3fb3b44..fe99e2f72 100644
--- a/agents-api/agents_api/activities/task_steps/base_evaluate.py
+++ b/agents-api/agents_api/activities/task_steps/base_evaluate.py
@@ -4,13 +4,33 @@
 from beartype import beartype
 from box import Box
 from openai import BaseModel
+from simpleeval import NameNotDefined
 from temporalio import activity
+from thefuzz import fuzz
 
 from ...common.storage_handler import auto_blob_store
 from ...env import testing
 from ..utils import get_evaluator
 
 
+class EvaluateError(Exception):
+    def __init__(self, error, expression, values):
+        error_message = error.message if hasattr(error, "message") else str(error)
+        message = error_message
+
+        # Catch a possible jinja template error
+        if "unhashable" in error_message and "{{" in expression:
+            message += "\nSuggestion: It seems like you used a jinja template, did you mean to use a python expression?"
+
+        # Catch a possible misspell in a variable name
+        if isinstance(error, NameNotDefined):
+            misspelledName = error_message.split("'")[1]
+            for variableName in values.keys():
+                if fuzz.ratio(variableName, misspelledName) >= 90.0:
+                    message += f"\nDid you mean '{variableName}' instead of '{misspelledName}'?"
+        super().__init__(message)
+
+
 @auto_blob_store
 @beartype
 async def base_evaluate(
@@ -47,22 +67,32 @@ async def base_evaluate(
 
     evaluator = get_evaluator(names=values, extra_functions=extra_lambdas)
 
+    chosen_expression = ""
+
     try:
         result = None
         match exprs:
             case str():
+                chosen_expression = exprs
                 result = evaluator.eval(exprs)
             case list():
-                result = [evaluator.eval(expr) for expr in exprs]
+                result = []
+                for expr in exprs:
+                    chosen_expression = expr
+                    result.append(evaluator.eval(expr))
             case dict() as d if all(
                 isinstance(v, dict) or isinstance(v, str) for v in d.values()
             ):
-                result = {
-                    k: {ik: evaluator.eval(iv) for ik, iv in v.items()}
-                    if isinstance(v, dict)
-                    else evaluator.eval(v)
-                    for k, v in d.items()
-                }
+                result = {}
+                for k, v in d.items():
+                    if isinstance(v, str):
+                        chosen_expression = v
+                        result[k] = evaluator.eval(v)
+                    else:
+                        result[k] = {}
+                        for k1, v1 in v.items():
+                            chosen_expression = v1
+                            result[k][k1] = evaluator.eval(v1)
             case _:
                 raise ValueError(f"Invalid expression: {exprs}")
 
@@ -71,7 +101,8 @@ async def base_evaluate(
     except BaseException as e:
         if activity.in_activity():
             activity.logger.error(f"Error in base_evaluate: {e}")
-        raise
+        newException = EvaluateError(e, chosen_expression, values)
+        raise newException from e
 
 
 # Note: This is here just for clarity. We could have just imported base_evaluate directly
diff --git a/agents-api/poetry.lock b/agents-api/poetry.lock
index 1f5c96c37..ca88522e3 100644
--- a/agents-api/poetry.lock
+++ b/agents-api/poetry.lock
@@ -4117,6 +4117,106 @@ files = [
 [package.dependencies]
 cffi = {version = "*", markers = "implementation_name == \"pypy\""}
 
+[[package]]
+name = "rapidfuzz"
+version = "3.10.0"
+description = "rapid fuzzy string matching"
+optional = false
+python-versions = ">=3.9"
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+    {file = "rapidfuzz-3.10.0-pp310-pypy310_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:20bd153aacc244e4c907d772c703fea82754c4db14f8aa64d75ff81b7b8ab92d"},
+    {file = "rapidfuzz-3.10.0-pp310-pypy310_pp73-win_amd64.whl", hash = "sha256:50484d563f8bfa723c74c944b0bb15b9e054db9c889348c8c307abcbee75ab92"},
+    {file = "rapidfuzz-3.10.0-pp39-pypy39_pp73-macosx_10_15_x86_64.whl", hash = "sha256:5897242d455461f2c5b82d7397b29341fd11e85bf3608a522177071044784ee8"},
+    {file = "rapidfuzz-3.10.0-pp39-pypy39_pp73-macosx_11_0_arm64.whl", hash = "sha256:116c71a81e046ba56551d8ab68067ca7034d94b617545316d460a452c5c3c289"},
+    {file = "rapidfuzz-3.10.0-pp39-pypy39_pp73-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:f0a547e4350d1fa32624d3eab51eff8cf329f4cae110b4ea0402486b1da8be40"},
+    {file = "rapidfuzz-3.10.0-pp39-pypy39_pp73-manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:399b9b79ccfcf50ca3bad7692bc098bb8eade88d7d5e15773b7f866c91156d0c"},
+    {file = "rapidfuzz-3.10.0-pp39-pypy39_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:7947a425d1be3e744707ee58c6cb318b93a56e08f080722dcc0347e0b7a1bb9a"},
+    {file = "rapidfuzz-3.10.0-pp39-pypy39_pp73-win_amd64.whl", hash = "sha256:94c48b4a2a4b1d22246f48e2b11cae01ec7d23f0c9123f8bb822839ad79d0a88"},
+    {file = "rapidfuzz-3.10.0.tar.gz", hash = "sha256:6b62af27e65bb39276a66533655a2fa3c60a487b03935721c45b7809527979be"},
+]
+
+[package.extras]
+all = ["numpy"]
+
 [[package]]
 name = "referencing"
 version = "0.35.1"
@@ -5001,6 +5101,20 @@ docs = ["myst-parser", "pydata-sphinx-theme", "sphinx"]
 test = ["pre-commit", "pytest (>=7.0)", "pytest-timeout"]
 typing = ["mypy (>=1.6,<2.0)", "traitlets (>=5.11.1)"]
 
+[[package]]
+name = "thefuzz"
+version = "0.22.1"
+description = "Fuzzy string matching in python"
+optional = false
+python-versions = ">=3.8"
+files = [
+    {file = "thefuzz-0.22.1-py3-none-any.whl", hash = "sha256:59729b33556850b90e1093c4cf9e618af6f2e4c985df193fdf3c5b5cf02ca481"},
+    {file = "thefuzz-0.22.1.tar.gz", hash = "sha256:7138039a7ecf540da323792d8592ef9902b1d79eb78c147d4f20664de79f3680"},
+]
+
+[package.dependencies]
+rapidfuzz = ">=3.0.0,<4.0.0"
+
 [[package]]
 name = "thinc"
 version = "8.3.2"
@@ -5957,4 +6071,4 @@ type = ["pytest-mypy"]
 [metadata]
 lock-version = "2.0"
 python-versions = ">=3.12,<3.13"
-content-hash = "6378447b12d87d1403ad5b9465b5fe7ed97b561b131d31eb52c85871da50449e"
+content-hash = "c1c4a3cbec01bd43e2f94bd7bca281642839d06dd33b6203e10659a4b9b2128d"
diff --git a/agents-api/pyproject.toml b/agents-api/pyproject.toml
index 910f9e53b..fdce646fb 100644
--- a/agents-api/pyproject.toml
+++ b/agents-api/pyproject.toml
@@ -45,6 +45,7 @@ xxhash = "^3.5.0"
 spacy = "^3.8.2"
 en-core-web-sm = {url = "https://github.com/explosion/spacy-models/releases/download/en_core_web_sm-3.8.0/en_core_web_sm-3.8.0-py3-none-any.whl"}
 msgpack = "^1.1.0"
+thefuzz = "^0.22.1"
 gunicorn = "^23.0.0"
 uvloop = "^0.21.0"
 [tool.poetry.group.dev.dependencies]